diff --git a/Sources/CLI/cmd/agent/AgentCommand.swift b/Sources/CLI/cmd/agent/AgentCommand.swift
index cc872af..739cc2b 100644
--- a/Sources/CLI/cmd/agent/AgentCommand.swift
+++ b/Sources/CLI/cmd/agent/AgentCommand.swift
@@ -1,6 +1,8 @@
 import ArgumentParser
 
-struct AgentCommand: ParsableCommand {
+struct AgentCommand: ParsableCommand, GlobalOptionsProviding {
+    @OptionGroup var global: GlobalOptions
+
     static let configuration = CommandConfiguration(
         commandName: "agent",
         abstract: "Agent mode utilities.",
diff --git a/Sources/CLI/cmd/agent/skills/AgentSkillsCommand.swift b/Sources/CLI/cmd/agent/skills/AgentSkillsCommand.swift
index 2c32474..ad093df 100644
--- a/Sources/CLI/cmd/agent/skills/AgentSkillsCommand.swift
+++ b/Sources/CLI/cmd/agent/skills/AgentSkillsCommand.swift
@@ -1,6 +1,8 @@
 import ArgumentParser
 
-struct AgentSkillsCommand: ParsableCommand {
+struct AgentSkillsCommand: ParsableCommand, GlobalOptionsProviding {
+    @OptionGroup var global: GlobalOptions
+
     static let configuration = CommandConfiguration(
         commandName: "skills",
         abstract: "Access portable Agent Skills bundled with apple-docs.",
diff --git a/Sources/CLI/cmd/agent/skills/AgentSkillsGetCommand.swift b/Sources/CLI/cmd/agent/skills/AgentSkillsGetCommand.swift
index 0f42069..d302620 100644
--- a/Sources/CLI/cmd/agent/skills/AgentSkillsGetCommand.swift
+++ b/Sources/CLI/cmd/agent/skills/AgentSkillsGetCommand.swift
@@ -5,7 +5,9 @@ import Logging
     @preconcurrency import SentrySwift
 #endif
 
-struct AgentSkillsGetCommand: ParsableCommand {
+struct AgentSkillsGetCommand: ParsableCommand, GlobalOptionsProviding {
+    @OptionGroup var global: GlobalOptions
+
     private static let logger = Logger(
         label: "com.techprimate.apple-docs.agent-skills-get"
     )
diff --git a/Sources/CLI/cmd/agent/skills/AgentSkillsInstallCommand.swift b/Sources/CLI/cmd/agent/skills/AgentSkillsInstallCommand.swift
index b412da8..fedd9bd 100644
--- a/Sources/CLI/cmd/agent/skills/AgentSkillsInstallCommand.swift
+++ b/Sources/CLI/cmd/agent/skills/AgentSkillsInstallCommand.swift
@@ -1,6 +1,8 @@
 import ArgumentParser
 
-struct AgentSkillsInstallCommand: ParsableCommand {
+struct AgentSkillsInstallCommand: ParsableCommand, GlobalOptionsProviding {
+    @OptionGroup var global: GlobalOptions
+
     static let configuration = CommandConfiguration(
         commandName: "install",
         abstract: "Install bundled Agent Skills into a .agents directory.",
diff --git a/Sources/CLI/cmd/agent/skills/AgentSkillsListCommand.swift b/Sources/CLI/cmd/agent/skills/AgentSkillsListCommand.swift
index 6156aad..25b68ac 100644
--- a/Sources/CLI/cmd/agent/skills/AgentSkillsListCommand.swift
+++ b/Sources/CLI/cmd/agent/skills/AgentSkillsListCommand.swift
@@ -5,7 +5,9 @@ import Logging
     @preconcurrency import SentrySwift
 #endif
 
-struct AgentSkillsListCommand: ParsableCommand {
+struct AgentSkillsListCommand: ParsableCommand, GlobalOptionsProviding {
+    @OptionGroup var global: GlobalOptions
+
     private static let logger = Logger(
         label: "com.techprimate.apple-docs.agent-skills-list"
     )
diff --git a/Sources/CLI/cmd/agent/skills/AgentSkillsUninstallCommand.swift b/Sources/CLI/cmd/agent/skills/AgentSkillsUninstallCommand.swift
index f8922d5..6f3683b 100644
--- a/Sources/CLI/cmd/agent/skills/AgentSkillsUninstallCommand.swift
+++ b/Sources/CLI/cmd/agent/skills/AgentSkillsUninstallCommand.swift
@@ -1,6 +1,8 @@
 import ArgumentParser
 
-struct AgentSkillsUninstallCommand: ParsableCommand {
+struct AgentSkillsUninstallCommand: ParsableCommand, GlobalOptionsProviding {
+    @OptionGroup var global: GlobalOptions
+
     static let configuration = CommandConfiguration(
         commandName: "uninstall",
         abstract: "Remove skills managed by apple-docs from a .agents directory.",
diff --git a/Sources/CLI/cmd/cache/CacheCleanCommand.swift b/Sources/CLI/cmd/cache/CacheCleanCommand.swift
index 35ef7d1..267d6af 100644
--- a/Sources/CLI/cmd/cache/CacheCleanCommand.swift
+++ b/Sources/CLI/cmd/cache/CacheCleanCommand.swift
@@ -5,7 +5,9 @@ import Logging
     @preconcurrency import SentrySwift
 #endif
 
-struct CacheCleanCommand: ParsableCommand {
+struct CacheCleanCommand: ParsableCommand, GlobalOptionsProviding {
+    @OptionGroup var global: GlobalOptions
+
     private static let logger = Logger(
         label: "com.techprimate.apple-docs.cache-clean"
     )
diff --git a/Sources/CLI/cmd/cache/CacheCommand.swift b/Sources/CLI/cmd/cache/CacheCommand.swift
index 31e77c0..158f037 100644
--- a/Sources/CLI/cmd/cache/CacheCommand.swift
+++ b/Sources/CLI/cmd/cache/CacheCommand.swift
@@ -1,6 +1,8 @@
 import ArgumentParser
 
-struct CacheCommand: ParsableCommand {
+struct CacheCommand: ParsableCommand, GlobalOptionsProviding {
+    @OptionGroup var global: GlobalOptions
+
     static let configuration = CommandConfiguration(
         commandName: "cache",
         abstract: "Manage cached Apple documentation.",
diff --git a/Sources/CLI/cmd/technologies/TechnologiesCommand.swift b/Sources/CLI/cmd/technologies/TechnologiesCommand.swift
index 55730d7..3a9cff0 100644
--- a/Sources/CLI/cmd/technologies/TechnologiesCommand.swift
+++ b/Sources/CLI/cmd/technologies/TechnologiesCommand.swift
@@ -1,6 +1,8 @@
 import ArgumentParser
 
-struct TechnologiesCommand: AsyncParsableCommand {
+struct TechnologiesCommand: AsyncParsableCommand, GlobalOptionsProviding {
+    @OptionGroup var global: GlobalOptions
+
     static let configuration = CommandConfiguration(
         commandName: "technologies",
         abstract: "Work with Apple documentation technologies.",
diff --git a/Sources/CLI/cmd/technologies/TechnologiesListCommand.swift b/Sources/CLI/cmd/technologies/TechnologiesListCommand.swift
index 737f7d3..1f8f2f7 100644
--- a/Sources/CLI/cmd/technologies/TechnologiesListCommand.swift
+++ b/Sources/CLI/cmd/technologies/TechnologiesListCommand.swift
@@ -5,7 +5,9 @@ import Logging
     @preconcurrency import SentrySwift
 #endif
 
-struct TechnologiesListCommand: AsyncParsableCommand {
+struct TechnologiesListCommand: AsyncParsableCommand, GlobalOptionsProviding {
+    @OptionGroup var global: GlobalOptions
+
     private static let logger = Logger(
         label: "com.techprimate.apple-docs.technologies-list"
     )
diff --git a/Sources/CLI/cmd/types/TypesCommand.swift b/Sources/CLI/cmd/types/TypesCommand.swift
index 423be34..504be6c 100644
--- a/Sources/CLI/cmd/types/TypesCommand.swift
+++ b/Sources/CLI/cmd/types/TypesCommand.swift
@@ -1,6 +1,8 @@
 import ArgumentParser
 
-struct TypesCommand: AsyncParsableCommand {
+struct TypesCommand: AsyncParsableCommand, GlobalOptionsProviding {
+    @OptionGroup var global: GlobalOptions
+
     static let configuration = CommandConfiguration(
         commandName: "types",
         abstract: "Work with Apple documentation types.",
diff --git a/Sources/CLI/cmd/types/TypesListCommand.swift b/Sources/CLI/cmd/types/TypesListCommand.swift
index 089eb12..4132942 100644
--- a/Sources/CLI/cmd/types/TypesListCommand.swift
+++ b/Sources/CLI/cmd/types/TypesListCommand.swift
@@ -5,7 +5,9 @@ import Logging
     @preconcurrency import SentrySwift
 #endif
 
-struct TypesListCommand: AsyncParsableCommand {
+struct TypesListCommand: AsyncParsableCommand, GlobalOptionsProviding {
+    @OptionGroup var global: GlobalOptions
+
     private static let logger = Logger(
         label: "com.techprimate.apple-docs.types-list"
     )
diff --git a/Sources/CLI/cmd/types/TypesSearchCommand.swift b/Sources/CLI/cmd/types/TypesSearchCommand.swift
index 1100652..28cbe68 100644
--- a/Sources/CLI/cmd/types/TypesSearchCommand.swift
+++ b/Sources/CLI/cmd/types/TypesSearchCommand.swift
@@ -5,7 +5,9 @@ import Logging
     @preconcurrency import SentrySwift
 #endif
 
-struct TypesSearchCommand: AsyncParsableCommand {
+struct TypesSearchCommand: AsyncParsableCommand, GlobalOptionsProviding {
+    @OptionGroup var global: GlobalOptions
+
     private static let logger = Logger(
         label: "com.techprimate.apple-docs.types-search"
     )
diff --git a/Sources/CLI/cmd/types/TypesViewCommand.swift b/Sources/CLI/cmd/types/TypesViewCommand.swift
index 427abfc..df7eae0 100644
--- a/Sources/CLI/cmd/types/TypesViewCommand.swift
+++ b/Sources/CLI/cmd/types/TypesViewCommand.swift
@@ -5,7 +5,9 @@ import Logging
     @preconcurrency import SentrySwift
 #endif
 
-struct TypesViewCommand: AsyncParsableCommand {
+struct TypesViewCommand: AsyncParsableCommand, GlobalOptionsProviding {
+    @OptionGroup var global: GlobalOptions
+
     private static let logger = Logger(
         label: "com.techprimate.apple-docs.types-view"
     )
diff --git a/Sources/CLI/main/AppleDocs.swift b/Sources/CLI/main/AppleDocs.swift
index 63ace2a..c3f28ce 100644
--- a/Sources/CLI/main/AppleDocs.swift
+++ b/Sources/CLI/main/AppleDocs.swift
@@ -4,7 +4,6 @@ import Logging
 
 #if canImport(SentrySwift)
     @preconcurrency import SentrySwift
-    import SentrySwiftLog
 #endif
 
 @main
@@ -14,21 +13,36 @@ enum AppleDocs {
     @MainActor
     static func main() async {
         let telemetryEnabled = configureTelemetry()
+        var loggingConfigured = false
 
         do {
             var command = try await CLI.asyncParseAsRoot()
+            LoggingConfiguration.bootstrap(
+                verbose: verboseLoggingEnabled(for: command),
+                telemetryEnabled: telemetryEnabled
+            )
+            loggingConfigured = true
+            Self.logger.debug("CLI command parsed")
             if var asyncCommand = command as? any AsyncParsableCommand {
                 try await asyncCommand.run()
             } else {
                 try command.run()
             }
+            Self.logger.debug("CLI command finished")
             finishTelemetry(enabled: telemetryEnabled)
         } catch {
+            if !loggingConfigured {
+                LoggingConfiguration.bootstrap(verbose: false, telemetryEnabled: telemetryEnabled)
+            }
             captureTelemetry(error, enabled: telemetryEnabled)
             CLI.exit(withError: error)
         }
     }
 
+    private static func verboseLoggingEnabled(for command: any ParsableCommand) -> Bool {
+        (command as? any GlobalOptionsProviding)?.global.verbose ?? false
+    }
+
     private static func configureTelemetry() -> Bool {
         #if canImport(SentrySwift)
             let enabled = SentryConfiguration.isEnabled(
@@ -38,19 +52,9 @@ enum AppleDocs {
                 SentrySDK.start { options in
                     SentryConfiguration.configure(options)
                 }
-                LoggingSystem.bootstrap { _ in
-                    SentryLogHandler(logLevel: .info)
-                }
-            } else {
-                LoggingSystem.bootstrap { _ in
-                    SwiftLogNoOpLogHandler()
-                }
             }
             return enabled
         #else
-            LoggingSystem.bootstrap { _ in
-                SwiftLogNoOpLogHandler()
-            }
             return false
         #endif
     }
diff --git a/Sources/CLI/main/CLI.swift b/Sources/CLI/main/CLI.swift
index 7271d4e..51e20ca 100644
--- a/Sources/CLI/main/CLI.swift
+++ b/Sources/CLI/main/CLI.swift
@@ -1,6 +1,8 @@
 import ArgumentParser
 
-struct CLI: AsyncParsableCommand {
+struct CLI: AsyncParsableCommand, GlobalOptionsProviding {
+    @OptionGroup var global: GlobalOptions
+
     static let configuration = CommandConfiguration(
         commandName: "apple-docs",
         abstract: "Access Apple developer documentation from the command line.",
diff --git a/Sources/CLI/main/GlobalOptions.swift b/Sources/CLI/main/GlobalOptions.swift
new file mode 100644
index 0000000..accb61d
--- /dev/null
+++ b/Sources/CLI/main/GlobalOptions.swift
@@ -0,0 +1,10 @@
+import ArgumentParser
+
+struct GlobalOptions: ParsableArguments {
+    @Flag(help: "Show debug and higher-level logs on stderr.")
+    var verbose = false
+}
+
+protocol GlobalOptionsProviding {
+    var global: GlobalOptions { get }
+}
diff --git a/Sources/CLI/main/LoggingConfiguration.swift b/Sources/CLI/main/LoggingConfiguration.swift
new file mode 100644
index 0000000..f9957d0
--- /dev/null
+++ b/Sources/CLI/main/LoggingConfiguration.swift
@@ -0,0 +1,40 @@
+import Logging
+
+#if canImport(SentrySwift)
+    import SentrySwiftLog
+#endif
+
+enum LoggingConfiguration {
+    static func bootstrap(verbose: Bool, telemetryEnabled: Bool) {
+        LoggingSystem.bootstrap { label in
+            var telemetry: (any LogHandler)?
+            #if canImport(SentrySwift)
+                if telemetryEnabled {
+                    telemetry = SentryLogHandler(logLevel: .info)
+                }
+            #endif
+            return handler(
+                console: StreamLogHandler.standardError(label: label),
+                telemetry: telemetry,
+                verbose: verbose
+            )
+        }
+    }
+
+    static func handler(
+        console: any LogHandler, telemetry: (any LogHandler)?, verbose: Bool
+    ) -> any LogHandler {
+        var handlers: [any LogHandler] = []
+        if verbose {
+            var console = console
+            console.logLevel = .debug
+            handlers.append(console)
+        }
+        if var telemetry {
+            telemetry.logLevel = .info
+            handlers.append(telemetry)
+        }
+        guard !handlers.isEmpty else { return SwiftLogNoOpLogHandler() }
+        return MultiplexLogHandler(handlers)
+    }
+}
diff --git a/Tests/CLITests/client/ClientLogRecorder.swift b/Tests/CLITests/client/ClientLogRecorder.swift
index 03416f3..340fe17 100644
--- a/Tests/CLITests/client/ClientLogRecorder.swift
+++ b/Tests/CLITests/client/ClientLogRecorder.swift
@@ -11,10 +11,14 @@ final class ClientLogRecorder: Sendable {
 
     func logger() -> Logger {
         Logger(label: "test.client") { _ in
-            RecordingHandler(recorder: self)
+            self.handler()
         }
     }
 
+    func handler() -> any LogHandler {
+        RecordingHandler(recorder: self)
+    }
+
     private func append(_ event: LogEvent) {
         storage.withLock { $0.append(event) }
     }
diff --git a/Tests/CLITests/main/CLITests.swift b/Tests/CLITests/main/CLITests.swift
index 0e040d8..8fab04d 100644
--- a/Tests/CLITests/main/CLITests.swift
+++ b/Tests/CLITests/main/CLITests.swift
@@ -4,6 +4,78 @@ import Testing
 
 @Suite("CLI help")
 struct CLITests {
+    @Test(
+        "accepts verbose at every command depth",
+        arguments: [
+            ["--verbose", "agent", "skills", "list"],
+            ["agent", "--verbose", "skills", "list"],
+            ["agent", "skills", "--verbose", "list"],
+            ["agent", "skills", "list", "--verbose"],
+        ])
+    func acceptsVerboseAtEveryDepth(arguments: [String]) throws {
+        // -- Arrange --
+        let expectedType = AgentSkillsListCommand.self
+
+        // -- Act --
+        let command = try CLI.parseAsRoot(arguments)
+
+        // -- Assert --
+        #expect(type(of: command) == expectedType)
+        let options = try #require(command as? any GlobalOptionsProviding)
+        #expect(options.global.verbose)
+    }
+
+    @Test(
+        "accepts verbose on each executable command",
+        arguments: [
+            ["types", "view", "String", "--technology", "Swift", "--json"],
+            ["types", "list", "--technology", "Swift", "--agent"],
+            ["types", "search", "String", "--technology", "Swift"],
+            ["technologies", "list", "--json"],
+            ["cache", "clean"],
+            ["agent", "skills", "get", "apple-docs"],
+            ["agent", "skills", "list"],
+            ["agent", "skills", "install", "apple-docs", "--dry-run"],
+            ["agent", "skills", "uninstall", "apple-docs", "--dry-run"],
+        ])
+    func acceptsVerboseOnEachCommand(arguments: [String]) throws {
+        // -- Arrange --
+        let arguments = arguments + ["--verbose"]
+
+        // -- Act --
+        let command = try CLI.parseAsRoot(arguments)
+
+        // -- Assert --
+        #expect(type(of: command).configuration.subcommands.isEmpty)
+        let options = try #require(command as? any GlobalOptionsProviding)
+        #expect(options.global.verbose)
+    }
+
+    @Test("does not treat positional values after the terminator as flags")
+    func respectsArgumentTerminator() throws {
+        // -- Arrange --
+        let arguments = ["agent", "skills", "get", "--", "--verbose"]
+
+        // -- Act --
+        let command = try #require(CLI.parseAsRoot(arguments) as? AgentSkillsGetCommand)
+
+        // -- Assert --
+        #expect(command.name == "--verbose")
+        #expect(!command.global.verbose)
+    }
+
+    @Test("leaves verbose disabled by default")
+    func defaultsToQuietLogging() throws {
+        // -- Arrange --
+        let arguments = ["agent", "skills", "list"]
+
+        // -- Act --
+        let command = try #require(CLI.parseAsRoot(arguments) as? AgentSkillsListCommand)
+
+        // -- Assert --
+        #expect(!command.global.verbose)
+    }
+
     @Test("directs agents to bundled skills")
     func includesAgentSkillsHint() {
         #expect(
diff --git a/Tests/CLITests/main/LoggingConfigurationTests.swift b/Tests/CLITests/main/LoggingConfigurationTests.swift
new file mode 100644
index 0000000..e3034fd
--- /dev/null
+++ b/Tests/CLITests/main/LoggingConfigurationTests.swift
@@ -0,0 +1,49 @@
+import Logging
+import Testing
+
+@testable import CLI
+
+@Suite("Global logging configuration")
+struct LoggingConfigurationTests {
+    @available(macOS 15, *)
+    @Test("verbose controls console logs independently of telemetry", arguments: [false, true])
+    func routesTelemetryIndependently(verbose: Bool) {
+        // -- Arrange --
+        let console = ClientLogRecorder()
+        let telemetry = ClientLogRecorder()
+        let logger = Logger(label: "test") { _ in
+            LoggingConfiguration.handler(console: console.handler(), telemetry: telemetry.handler(), verbose: verbose)
+        }
+
+        // -- Act --
+        for level in [Logger.Level.trace, .debug, .info, .notice, .warning, .error, .critical] {
+            logger.log(level: level, "Test event", metadata: ["request": "test"])
+        }
+
+        // -- Assert --
+        let expectedConsole: [Logger.Level] = verbose ? [.debug, .info, .notice, .warning, .error, .critical] : []
+        #expect(console.events.map(\.level) == expectedConsole)
+        #expect(telemetry.events.map(\.level) == [.info, .notice, .warning, .error, .critical])
+        #expect(telemetry.events.allSatisfy { $0.metadata?["request"]?.description == "test" })
+    }
+
+    @available(macOS 15, *)
+    @Test("verbose works with telemetry disabled and stays quiet by default", arguments: [false, true])
+    func routesWithoutTelemetry(verbose: Bool) {
+        // -- Arrange --
+        let console = ClientLogRecorder()
+        let logger = Logger(label: "test") { _ in
+            LoggingConfiguration.handler(console: console.handler(), telemetry: nil, verbose: verbose)
+        }
+
+        // -- Act --
+        for level in [Logger.Level.trace, .debug, .info, .notice, .warning, .error, .critical] {
+            logger.log(level: level, "Test event", metadata: ["request": "test"])
+        }
+
+        // -- Assert --
+        let expected: [Logger.Level] = verbose ? [.debug, .info, .notice, .warning, .error, .critical] : []
+        #expect(console.events.map(\.level) == expected)
+        #expect(console.events.allSatisfy { $0.metadata?["request"]?.description == "test" })
+    }
+}